NZ287862A - Preparation of <alpha>-methoxyiminocarboxylic acid methylamides by pinner reaction of <alpha>-ketonitriles, oxime formation and methylation - Google Patents
Preparation of <alpha>-methoxyiminocarboxylic acid methylamides by pinner reaction of <alpha>-ketonitriles, oxime formation and methylationInfo
- Publication number
- NZ287862A NZ287862A NZ287862A NZ28786295A NZ287862A NZ 287862 A NZ287862 A NZ 287862A NZ 287862 A NZ287862 A NZ 287862A NZ 28786295 A NZ28786295 A NZ 28786295A NZ 287862 A NZ287862 A NZ 287862A
- Authority
- NZ
- New Zealand
- Prior art keywords
- alpha
- methylation
- ketonitriles
- preparation
- pinner reaction
- Prior art date
Links
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 title abstract 4
- 238000003482 Pinner synthesis reaction Methods 0.000 title abstract 2
- 239000002253 acid Substances 0.000 title abstract 2
- 230000011987 methylation Effects 0.000 title abstract 2
- 238000007069 methylation reaction Methods 0.000 title abstract 2
- 150000002923 oximes Chemical class 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000002360 preparation method Methods 0.000 title 1
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- GTBRTGPZZALPNS-MXHVRSFHSA-N cyanoketone Chemical compound C1C=C2C(C)(C)C(=O)[C@H](C#N)C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@](C)(O)[C@@]1(C)CC2 GTBRTGPZZALPNS-MXHVRSFHSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D249/12—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/70—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/72—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms
- C07C235/76—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C235/78—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups and doubly-bound oxygen atoms bound to the same carbon skeleton with the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/08—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reaction of hydroxylamines with carbonyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/50—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals
- C07C251/60—Oximes having oxygen atoms of oxyimino groups bound to carbon atoms of substituted hydrocarbon radicals of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/18—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group
- C07C67/22—Preparation of carboxylic acid esters by conversion of a group containing nitrogen into an ester group from nitriles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process and intermediates for preparing alpha -methoxyiminocarboxylic acid methylamides (I) by Pinner reaction of a cyanoketone (II) with an alcohol and subsequent reaction of the resulting ester (IV) with hydroxylamine to give the oxime (V), methylation of (V) to give the oxime ether (VI) and subsequent reaction of (VI) with methylamine: <IMAGE> <IMAGE> +TR <IMAGE> X = nitro, trifluoromethyl, halogen, alkyl or alkoxy; n = 0, 1, 2, 3 or 4; Y = a C-organic radical.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4420416 | 1994-06-10 | ||
| PCT/EP1995/002013 WO1995034526A1 (en) | 1994-06-10 | 1995-05-26 | METHOD OF PREPARING α-METHOXYIMINOCARBOXYLIC ACID METHYLAMIDES, AND INTERMEDIATES USED IN THE METHOD |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ287862A true NZ287862A (en) | 1999-02-25 |
Family
ID=6520340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ287862A NZ287862A (en) | 1994-06-10 | 1995-05-26 | Preparation of <alpha>-methoxyiminocarboxylic acid methylamides by pinner reaction of <alpha>-ketonitriles, oxime formation and methylation |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US5856560A (en) |
| EP (1) | EP0765304B2 (en) |
| JP (1) | JP4114948B2 (en) |
| KR (2) | KR100374949B1 (en) |
| CN (1) | CN1082503C (en) |
| AT (1) | ATE183176T1 (en) |
| AU (1) | AU686821B2 (en) |
| BG (1) | BG63115B1 (en) |
| BR (1) | BR9507979A (en) |
| CA (1) | CA2192594C (en) |
| CZ (1) | CZ297235B6 (en) |
| DE (1) | DE59506598D1 (en) |
| DK (1) | DK0765304T4 (en) |
| ES (1) | ES2135741T5 (en) |
| FI (1) | FI120583B (en) |
| GE (1) | GEP20012438B (en) |
| GR (1) | GR3031313T3 (en) |
| HU (1) | HU219195B (en) |
| IL (1) | IL114038A (en) |
| MX (1) | MX9606276A (en) |
| NO (1) | NO307333B1 (en) |
| NZ (1) | NZ287862A (en) |
| PL (1) | PL179861B1 (en) |
| RU (1) | RU2146247C1 (en) |
| SK (1) | SK283068B6 (en) |
| UA (1) | UA42776C2 (en) |
| WO (1) | WO1995034526A1 (en) |
| ZA (1) | ZA954825B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4305502A1 (en) * | 1993-02-23 | 1994-08-25 | Basf Ag | Ortho-substituted 2-methoxyiminophenylacetic acid methylamides |
| CZ291625B6 (en) * | 1994-01-05 | 2003-04-16 | Bayer Aktiengesellschaft | Oxime derivatives |
| JPH07238701A (en) * | 1994-02-28 | 1995-09-12 | Koji Sakata | Sky parking space |
| DK0781764T3 (en) * | 1994-09-06 | 2000-07-10 | Shionogi & Co | Process for the preparation of alkoxyiminoacetamide derivatives |
| DE19540361A1 (en) | 1995-10-30 | 1997-05-07 | Basf Ag | Phenylacetic acid derivatives, processes and intermediates for their preparation and their use for controlling harmful fungi and animal pests |
| JP2000500766A (en) * | 1995-11-29 | 2000-01-25 | ノバルティス アクチェンゲゼルシャフト | Preparation of methoxyiminophenyl glycolic acid derivatives |
| CZ173198A3 (en) * | 1995-12-07 | 1998-08-12 | Novartis Ag | Process for preparing pesticides |
| HUP9900091A3 (en) * | 1995-12-07 | 2002-01-28 | Bayer Ag | Pesticides |
| EP0782982B1 (en) * | 1996-01-03 | 2000-05-17 | Novartis AG | Process for the preparation of o-chloro-methyl-phenylglyoxylic acid derivatives |
| FR2773155B1 (en) * | 1997-12-29 | 2000-01-28 | Rhone Poulenc Agrochimie | NEW FUNGICIDAL COMPOUNDS |
| AU2957899A (en) * | 1998-03-26 | 1999-10-18 | Shionogi & Co., Ltd. | Process for producing oxime compound |
| US6313344B1 (en) | 1998-05-27 | 2001-11-06 | Bayer Aktiengesellschaft | Organic compounds |
| WO2009037230A2 (en) * | 2007-09-17 | 2009-03-26 | Dsm Fine Chemicals Austria Nfg Gmbh & Co Kg | Improved process for preparing (e)-2-(2-chloromethylphenyl)-2-alkoximinoacetic esters |
| BRPI1005352A2 (en) * | 2009-02-05 | 2016-02-10 | Basf Se | processes for the production of 2-halogenomethylphenyl acetic acid derivatives, process for the production of an alkyloxime, process for the production of an oxime, use of 3-isochromanone and process for the production of one of a strobilurin fungicide |
| CN109912417A (en) * | 2018-12-29 | 2019-06-21 | 京博农化科技有限公司 | A kind of 2-(2- methylenedioxy phenoxy methyl)-methyl benzoylformate synthetic method |
Family Cites Families (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8617648D0 (en) † | 1986-07-18 | 1986-08-28 | Ici Plc | Fungicides |
| YU47288B (en) † | 1987-07-11 | 1995-01-31 | Schering Agrochemicals Limited | ACRYLATE FUNGICIDES AND THE PROCEDURE FOR THEIR PRODUCTION |
| DE3827361A1 (en) † | 1988-08-12 | 1990-03-01 | Basf Ag | OXIMETHER, METHOD FOR THE PRODUCTION THEREOF AND FUNGICIDES CONTAINING THESE COMPOUNDS |
| ES2054025T5 (en) * | 1988-11-21 | 1998-02-16 | Zeneca Ltd | FUNGICIDES. |
| DE3843439A1 (en) † | 1988-12-23 | 1990-06-28 | Basf Ag | SULFURIZED OXIMETERS AND FUNGICIDES CONTAINING THEM |
| EP0629609B1 (en) * | 1989-05-17 | 1996-12-04 | SHIONOGI SEIYAKU KABUSHIKI KAISHA trading under the name of SHIONOGI & CO. LTD. | Process for the preparation of Alkoxyiminoacetamide derivatives and an intermediate therefor |
| DE3933891A1 (en) * | 1989-10-11 | 1991-04-18 | Basf Ag | PHENYL ACETIC DERIVATIVES AND FUNGICIDES CONTAINING THEM |
| DE4009616A1 (en) * | 1990-03-26 | 1991-10-02 | Henkel Kgaa | LIQUID BODY CLEANER |
| PH11991042549B1 (en) * | 1990-06-05 | 2000-12-04 | ||
| DK0463488T4 (en) † | 1990-06-27 | 2004-05-10 | Basf Ag | O-benzyloxymeters and plant protection agents containing these compounds |
| DE4030038A1 (en) * | 1990-09-22 | 1992-03-26 | Basf Ag | New 2-substd. phenyl-acetamide derivs. - useful as fungicides, insecticides, acaricides and nematocides |
| DE4042271A1 (en) * | 1990-12-31 | 1992-07-02 | Basf Ag | Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s) |
| DK0712835T3 (en) * | 1990-12-31 | 1997-09-15 | Basf Ag | Process for preparing alpha-ketocarboxylic acid esters |
| DE4042280A1 (en) * | 1990-12-31 | 1992-07-02 | Basf Ag | Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s) |
| DE4042273A1 (en) * | 1990-12-31 | 1992-07-02 | Basf Ag | Prepn. of E-oxime ether(s) of phenyl-glyoxylic acid ester(s) |
| EP0569384B2 (en) * | 1991-01-30 | 2000-10-04 | Zeneca Limited | Fungicides |
| GB9218541D0 (en) * | 1991-09-30 | 1992-10-14 | Ici Plc | Fungicides |
| GB9122098D0 (en) * | 1991-10-17 | 1991-11-27 | Ici Plc | Fungicides |
| DE4203170A1 (en) * | 1992-02-05 | 1993-08-12 | Basf Ag | METHOD FOR PRODUCING E-OXIMETHERS OF PHENYLGLYOXYL ACID ESTERS |
| IL105191A (en) * | 1992-04-04 | 1998-08-16 | Basf Ag | 0-Iminooxymethylbenzoic acids and their preparation |
| DE59309100D1 (en) * | 1992-07-15 | 1998-12-03 | Basf Ag | Substituted oxime ethers and their use to control pests |
| IL106473A0 (en) * | 1992-08-11 | 1993-11-15 | Basf Ag | Acetylene derivatives and crop protection agents containing them |
| ES2094432T3 (en) * | 1992-08-29 | 1997-01-16 | Basf Ag | N-METHYLAMIDES, PROCEDURES AND INTERMEDIATE PRODUCTS FOR THEIR OBTAINING AS WELL AS A PROCEDURE FOR THE FIGHT AGAINST PESTS. |
| GB9221584D0 (en) * | 1992-10-14 | 1992-11-25 | Ici Plc | Chemical process |
| DE4238260A1 (en) * | 1992-11-12 | 1994-05-19 | Basf Ag | Substituted ortho-ethenylphenylacetic acid derivatives |
| GB9226734D0 (en) * | 1992-12-22 | 1993-02-17 | Ici Plc | Fungicides |
| DE4305502A1 (en) * | 1993-02-23 | 1994-08-25 | Basf Ag | Ortho-substituted 2-methoxyiminophenylacetic acid methylamides |
| US5506358A (en) * | 1993-03-16 | 1996-04-09 | Shionogi & Co., Ltd. | Process for producing alkoxyiminoacetamide compounds |
| DE69406483T2 (en) * | 1993-03-19 | 1998-03-19 | Ube Industries | Oxime ether compounds, process for their preparation and fungicides containing them |
| DE4310143A1 (en) * | 1993-03-29 | 1994-10-06 | Basf Ag | Imino-substituted phenylacetic acid amides, their preparation and fungicides containing them |
| JPH08319265A (en) † | 1995-05-23 | 1996-12-03 | Mitsubishi Chem Corp | Process for producing N-methyl-methoxyiminoacetic acid amide derivative and intermediate thereof |
-
1995
- 1995-05-26 CZ CZ0357896A patent/CZ297235B6/en not_active IP Right Cessation
- 1995-05-26 KR KR1019960707049A patent/KR100374949B1/en not_active Expired - Lifetime
- 1995-05-26 WO PCT/EP1995/002013 patent/WO1995034526A1/en not_active Ceased
- 1995-05-26 AU AU26710/95A patent/AU686821B2/en not_active Ceased
- 1995-05-26 MX MX9606276A patent/MX9606276A/en unknown
- 1995-05-26 UA UA97010107A patent/UA42776C2/en unknown
- 1995-05-26 EP EP95921761A patent/EP0765304B2/en not_active Expired - Lifetime
- 1995-05-26 SK SK1575-96A patent/SK283068B6/en not_active IP Right Cessation
- 1995-05-26 CA CA002192594A patent/CA2192594C/en not_active Expired - Fee Related
- 1995-05-26 DE DE59506598T patent/DE59506598D1/en not_active Expired - Lifetime
- 1995-05-26 JP JP50154296A patent/JP4114948B2/en not_active Expired - Lifetime
- 1995-05-26 HU HU9603401A patent/HU219195B/en not_active IP Right Cessation
- 1995-05-26 RU RU97100673A patent/RU2146247C1/en not_active IP Right Cessation
- 1995-05-26 GE GE2653A patent/GEP20012438B/en unknown
- 1995-05-26 NZ NZ287862A patent/NZ287862A/en not_active IP Right Cessation
- 1995-05-26 AT AT95921761T patent/ATE183176T1/en active
- 1995-05-26 ES ES95921761T patent/ES2135741T5/en not_active Expired - Lifetime
- 1995-05-26 DK DK95921761T patent/DK0765304T4/en active
- 1995-05-26 BR BR9507979A patent/BR9507979A/en not_active IP Right Cessation
- 1995-05-26 CN CN95194276A patent/CN1082503C/en not_active Expired - Lifetime
- 1995-05-26 PL PL95317712A patent/PL179861B1/en not_active IP Right Cessation
- 1995-06-07 IL IL11403895A patent/IL114038A/en not_active IP Right Cessation
- 1995-06-12 ZA ZA954825A patent/ZA954825B/en unknown
-
1996
- 1996-12-05 FI FI964901A patent/FI120583B/en not_active IP Right Cessation
- 1996-12-09 NO NO965259A patent/NO307333B1/en not_active IP Right Cessation
- 1996-12-10 US US08/750,822 patent/US5856560A/en not_active Expired - Lifetime
- 1996-12-10 KR KR19967007049A patent/KR970703931A/en active Granted
- 1996-12-28 BG BG101079A patent/BG63115B1/en unknown
-
1999
- 1999-09-22 GR GR990402413T patent/GR3031313T3/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) | ||
| ERR | Error or correction |
Free format text: THE OWNER HAS BEEN CORRECTED TO 3004745, BASF SE, CARL-BOSCH-STRASSE 38, 67056 LUDWIGSHAFEN, DE Effective date: 20141118 |
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| EXPY | Patent expired |